Imido transfer of sulfonylimino-λ3-bromane makes possible the synthesis of sulfonylimino-λ3-iodanes

Masahito Ochiai; Aiko Nakano; Akira Yoshimura; Kazunori Miyamoto; Satoko Hayashi; Waro Nakanishi

doi:10.1039/B818489E

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Imido transfer of sulfonylimino-λ³-bromane makes possible the synthesis of sulfonylimino-λ³-iodanes†

Masahito Ochiai,*^a Aiko Nakano,^a Akira Yoshimura,^a Kazunori Miyamoto,^a Satoko Hayashi^b and Waro Nakanishi*^b

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* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima, Japan
E-mail: mochiai@ph.tokushima-u.ac.jp
Fax: +81 88-633-9504

^b Department of Materials Science and Chemistry, Faculty of Systems Engineering, Wakayama University, 930 Sakaedani, Wakayama, Japan
E-mail: nakanisi@sys.wakayama-u.ac.jp
Fax: +8173-457-8253

Abstract

Sulfonylimino-λ³-bromane functions as a reactive nitrenoid, because of the hyperleaving group ability of aryl-λ³-bromanyl groups, and undergoes transimidations to iodobenzenes at room temperature under metal-free conditions probably via an S_N2-type nitrenoid transition state, yielding sulfonylimino-λ³-iodanes.

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Article information

DOI: https://doi.org/10.1039/B818489E
Article type: Communication
Submitted: 20 Oct 2008
Accepted: 10 Dec 2008
First published: 14 Jan 2009

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Chem. Commun., 2009, 959-961

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Imido transfer of sulfonylimino-λ³-bromane makes possible the synthesis of sulfonylimino-λ³-iodanes

M. Ochiai, A. Nakano, A. Yoshimura, K. Miyamoto, S. Hayashi and W. Nakanishi, Chem. Commun., 2009, 959 DOI: 10.1039/B818489E

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